ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE

Nihal KUŞ (Fizik Bölümü, Fen Fakültesi, Eskişehir Teknik Üniversitesi, 26470, Eskişehir, Türkiye)
Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler
3 1
Yıl: 2021 Cilt: 9 Sayı: ICONAT Special Issue Sayfa Aralığı: 74 - 84 Metin Dili: İngilizce DOI: 10.20290/estubtdb.1015146 İndeks Tarihi: 15-06-2022

ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE

Öz:
Quinolines are aromatic compounds consisting of benzene rings with a pyridine heterocyclic system. In this study, the structure and orbital interactions of the methyl 5-6 dihydro benzo(h) quinolone-4-carboxylate (MDQC) molecule, which is a quinoline derivative, were analyzed. In the calculation using the B3LYP/6-311++g(d,p) level, three conformers were found in the minimum energy state according to the O=C-O-C dihedral angle scan. The energy difference (E+ZPV) between the conformers was calculated ca. 1.9 and 34.8 kJ mol-1, respectively. The relative stability of the conformers was explained using the natural bond orbital (NBO) method and performed. The Fock matrix equation calculated donor and acceptor pairs and orbital energies for NBO pairs for the most stable conformer (MDQC-1). Dominant orbital interactions of selected NBOs for MDQC-1 were calculated at the theory level B3LYP/6-311++g(d,p) and plotted. The molecular electrostatic potential (MEP) surfaces were calculated by the DFT/B3LYP/6-311++g(d,p) method and drawn. NBO charges were calculated for MDQC-1 and MDQC-2 and analyzed
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • [1] Foley M, Tilley L. Quinoline Antimalarials: Mechanisms of Action and Resistance and Prospects for New Agents. Pharmacol Ther 1998;79: 55−87.
  • [2] Acton QA, Ed Antimalarial Quinolines: Advances in Research and Application, 2012 ed.; Scholarly Eds: Atlanta, GA, USA, 2013.
  • [3] Vlok MC. Artemisinin-Quinoline Hybrids: Design, Synthesis and Antimalarial Activity. Ph.D. Thesis, North-West University, Potchefstroom, 2013.
  • [4] Vargas LY, Castelli MV, Kouznetsov VV, Urbina JM, Lopez SN, Sortino M, Enriz RD, Ribas JC, Zacchino S. In vitro Antifungal Activity of New Series of Homoallylamines and Related Compounds with Inhibitory Properties of the Synthesis of Fungal Cell Wall Polymers. Bioorg Med Chem 2003; 11: 1531−1550.
  • [5] Ablordeppey SY, Fan P, Li S, Clark AM, Hufford CD. Substituted Indoloquinolines as New Antifungal Agents. Bioorg Med Chem 2002; 10: 1337−1346.
  • [6] Madapa S, Tusi Z, Batra S. Advances in the Synthesis of Quinoline and Quinoline-Annulated Ring Systems Curr Org Chem 2008; 12: 1116−1183.
  • [7] Vandekerckhove S and D'hooghe M. Quinoline-based antimalarial hybrid compounds. Bioorg Med Chem 2015; 23: 5098–5119.
  • [8] Lyon MA, Lawrence S, William JD and Jackson YA. Synthesis and structure verification of an analog of kuanoniamine. A J Chem Soc Perkin Trans 1999; 1: 437–442.
  • [9] World Health Organization. Guidelines for the Treatment of Malaria, Second ed; World Health Organization: Geneva, 2010.
  • [10] Dorndorp A, Nosten F, Stepniewska K, Day N, White N. South East Asian Quinine Artesunate Malaria Trial (SEAQUAMAT) Group. Artesunate versus Quinine for Treatment of Severe Falciparum Malaria: A Randomised Trial Lancet 2005; 366: 717−25.
  • [11] Gregory SB. Origins of the Quinolone Class of Antibacterials: An Expanded “Discovery Story. J Med Chem 2015; 58(12): 4874–4882.
  • [12] Całus S, Gondek E, Danel A, Jarosz B, Pokładko M, Kityk AV. Electro-luminescence of 6-R- 1,3-diphenyl-1H-Pyrazolo[3,4-b]quinoline-based Organic Light-Emitting Diodes (R= F, Br, Cl, CH3, C2H3 and N(C6H5)2). Mater Lett 2007; 61: 3292−3295.
  • [13] Caeiro G, Lopes JM, Magnoux P, Ayrault P and Ramoa Ribeiro FJ. A FT-IR Study of Deactivation Phenomena in Catalytic Cracking: Nitrogen Poisoning, Coke Formation, and Acidity-activity.Correlations. J Catal 2007; 249: 234−243.
  • [14] Paton JH, Reeves DS. Fluoroquinolone antibiotics. Microbiology, pharmacokinetics, and clinical use. Drugs. 1988; 36(2): 193−228.
  • [15] Gordon GR and Walter AJ. Synthesis of Substituted Quinolines and 5,6-Benzoquinolines. J Am Chem Soc 1939; 61; 2890−2895.
  • [16] Kuş N, Sagdinc S, Fausto R. Infrared Spectrum and UV-Induced Photochemistry of Matrix- Isolated 5-Hydroxyquinoline. J Phys Chem A 2015; 119(24): 6296−308.
  • [17] Kuş N, Henriques MS, Paixão JS, Lapinski L, and Fausto R. Crystal Structure, Matrix-Isolation FTIR, and UV-Induced Conformational Isomerization of 3-Quinolinecarboxaldehyde. J Phys Chem A 2014; 118 (38): 8708−8716.
  • [18] Horta P, Henriques MSC, Kuş N, Paixão JA, O'Neill PM, Cristiano MLS, Fausto R. Synthesis, structural and conformational analysis, and IR spectra of ethyl 4-chloro-7-iodoquinoline-3- carboxylate. Tetrahedron 2015; 71: 7583−7592.
  • [19] Horta P, Kuş N, Henriques MS, Paixão JA, Coelho L, Nogueira F, O'Neill PM, Fausto R, Cristiano ML. Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure to Retain Antimalarial Activity. J Org Chem 2015; 80(24): 12244−57.
  • [20] Frisch MJ et al. Gaussian 09, Revision A.0.2. Gaussian Inc, Wallingford CT, 2009. [21] Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior, Phys Rev A 1988; 38: 3098−3100
  • 22] Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785−789.
  • [23] Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor- acceptor viewpoint. Chem Rev 1988; 88: 899−926.
  • [24] Davies JE, Andrew DB. Quinoline. Acta Cryst 2001; E57: o947−o949.
  • [25] Kuş N, Reva I, Fausto R. Photoisomerization and photochemistry of matrix-isolated 3- furaldehyde. J Phys Chem A 2010; 114(47): 12427−36.
  • [26] Weinhold F, Landis CR. Valency and Bonding. A Natural Bond Orbital Donor-Acceptor Perspective. Cambridge University Press: New York, 2005
APA Kus N (2021). ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. , 74 - 84. 10.20290/estubtdb.1015146
Chicago Kus Nihal ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. (2021): 74 - 84. 10.20290/estubtdb.1015146
MLA Kus Nihal ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. , 2021, ss.74 - 84. 10.20290/estubtdb.1015146
AMA Kus N ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. . 2021; 74 - 84. 10.20290/estubtdb.1015146
Vancouver Kus N ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. . 2021; 74 - 84. 10.20290/estubtdb.1015146
IEEE Kus N "ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE." , ss.74 - 84, 2021. 10.20290/estubtdb.1015146
ISNAD Kus, Nihal. "ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE". (2021), 74-84. https://doi.org/10.20290/estubtdb.1015146
APA Kus N (2021). ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler, 9(ICONAT Special Issue), 74 - 84. 10.20290/estubtdb.1015146
Chicago Kus Nihal ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler 9, no.ICONAT Special Issue (2021): 74 - 84. 10.20290/estubtdb.1015146
MLA Kus Nihal ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler, vol.9, no.ICONAT Special Issue, 2021, ss.74 - 84. 10.20290/estubtdb.1015146
AMA Kus N ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler. 2021; 9(ICONAT Special Issue): 74 - 84. 10.20290/estubtdb.1015146
Vancouver Kus N ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler. 2021; 9(ICONAT Special Issue): 74 - 84. 10.20290/estubtdb.1015146
IEEE Kus N "ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE." Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler, 9, ss.74 - 84, 2021. 10.20290/estubtdb.1015146
ISNAD Kus, Nihal. "ORBITAL INTERACTIONS AND STABILIZATION ENERGIES OF METHYL 5-6 DIHYDRO BENZO(H) QUINOLINE-4-CARBOXYLATE". Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi b- Teorik Bilimler 9/ICONAT Special Issue (2021), 74-84. https://doi.org/10.20290/estubtdb.1015146
Sayfa Oluşturulma Tarihi
18-04-2024 0:53

İLETİŞİM

TÜBİTAK ULAKBİM TR Dizin

Yüzüncüyıl, İşçi Blokları Mahallesi

Muhsin Yazıcıoğlu Caddesi No:51/C

06530 Çankaya / ANKARA +90 (312) 298 92 00

trdizin@tubitak.gov.tr

TÜBİTAK ULAKBİM Ulusal Akademik Ağ ve Bilgi Merkezi Cahit Arf Bilgi Merkezi © Tüm Hakları Saklıdır. Gizlilik Politikası Kullanım Şartları